AU8542198A - Use of di- and oligoacylaromats for colouring fibres containing keratin - Google Patents
Use of di- and oligoacylaromats for colouring fibres containing keratin Download PDFInfo
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- AU8542198A AU8542198A AU85421/98A AU8542198A AU8542198A AU 8542198 A AU8542198 A AU 8542198A AU 85421/98 A AU85421/98 A AU 85421/98A AU 8542198 A AU8542198 A AU 8542198A AU 8542198 A AU8542198 A AU 8542198A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/415—Aminophenols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
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- Emergency Medicine (AREA)
- Cosmetics (AREA)
Description
1 Use of Di- and Oligoacylaromats for Colouring Fibres Containing Keratin This invention relates to the use of aromatic di- and oligoacyl compounds for colouring keratin containing fibres, more especially human hair, to a preparation containing aromatic di- and oligoacyl compounds for colouring keratin-containing fibres and to a process for colouring keratin-containing 5 fibres. In general, keratin-containing fibres, for example hair, wool or pelts, are dyed either with substantive dyes or with oxidation dyes which are formed by oxidative coupling of one or more primary intermediates with one another or with one or more secondary intermediates. Primary and secondary intermediates are also known as oxidation dye precursors. 10 The primary intermediates normally used are primary aromatic amines containing another free or substituted or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazolone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof. Special representatives are, for example, p-phenylenediamine, p-toluylenediamine, p aminophenol, o-aminophenol, 1-(2'-hydroxyethyl)-2,5-diaminobenzene, N,N-bis-(2-hydroxyethyl)-p 15 phenylenediamine, 2-(2,5-diaminophenoxy)-ethanol, 1 -phenyl-3-carboxyamido-4-amino-5-pyrazolone, 4-amino-3-methylphenol, 2,4,5,6-tetraaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 4 hydroxy-2,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2-dimethylamino-4,5,6 triaminopyrimidine, 2-hydroxyethylaminomethyl-4-aminophenol, 4,4'-diaminodiphenylamine, 4-amino 3-fluorophenol, 2-aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, bis-(2-hydroxy-5 20 aminophenyl)-methane, 1,4-bis-(4-aminophenyl)-diazacycloheptane, 1,3-bis-(N-(2-hydroxyethyl)-N-(4 aminophenylamino))-2-propanol, 4-amino-2-(2-hydroxyethoxy)-pheno and 4,5-diaminopyrazole derivatives according to EP 0 740 741 or WO 94/08970, for example 4,5-diamino-1-(2'-hydroxyethyl) pyrazole. The secondary intermediates used are generally m-phenylenediamine derivatives, naphthols, 25 resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols. Particularly suitable secondary intermediates are 1-naphthol, pyrogallol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, o aminophenol, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m phenylenediamine, 1-phenyl-3-methyl-5-pyrazolone, 2,4-dichloro-3-aminophenol, 1,3-bis-(2,4 diaminophenoxy)-propane, 4-chlororesorcinol, 2-chloro-6-methyl-3-aminophenol, 2-methyl resorcinol, 30 5-methyl resorcinol, 2,5-dimethylresorcinol, 2,6-dihydroxypyridine, 2,6-diaminopyridine, 2-amino-3 hydroxypyridine, 2,6-dihydroxy-3,4-diaminopyridine, 3-amino-2-methylamino-6-methoxypyridine, 4 amino-2-hydroxytoluene, 2,6-bis-(2-hydroxyethylamino)-toluene, 2,4-diaminophenoxyethanol, 1 methoxy-2-amino-4-(2-hydroxyethylamino)-benzene, 2-methyl-4-chloro-5-aminophenol, 6-methyl 1,2,3,4-tetrahydroquinoxaline, 3,4-methylenedioxyphenol, 3,4-methylenedioxyaniline, 2,6-dimethyl-3 35 aminophenol, 3-amino-6-methoxy-2-methylaminophenol, 2-hydroxy-4-aminophenoxyethanol, 2 methyl-5-(2-hydroxyethylamino)-pheno and 2,6-dihydroxy-3,4-dimethyl pyridine. With regard to the dyes suitable for use in the hair colouring and tinting formulations according to the invention, reference is also specifically made to Ch. Zviak's work The Science of Hair Care, Chapter 7 (pages 248-250; Substantive Dyes) and Chapter 8, pages 264-267; Oxidation Dye 40 Precursors), published as Vol. 7 of the Series "Dermatology" (Editors: Ch. Culnan and H. Maibach), 2 Marcel Dekker Inc., New York/Basel, 1986 and to the "Europiische Inventar der Kosmetik Rohstoffe" published by the Europsische Gemeinschaft and available in diskette form from the Bundesverband Deutscher Industrie- und Handelsunternehmen fOr Arzneimittel, Reformwaren und K6rperpflegemittel e.V., Mannheim, Germany. 5 Although intensive colours with good fastness properties can be obtained with oxidation dyes, the colour is generally developed under the influence of oxidising agents, such as H 2 02 for example, which in some cases can result in damage to the fibres. In addition, some oxidation dye precursors or certain mixtures of oxidation dye precursors can occasionally have a sensitising effect in people with sensitive skin. Although substantive dyes are applied under more moderate conditions, their 10 disadvantage is that, in many cases, the colours obtained have inadequate fastness properties. US 3,158,542 describes systems for colouring keratin-containing fibres which contain 1,2 diacetylbenzenes or aliphatic 1,2-diacetyl compounds in combination with amines, such as amino acids and aliphatic or aromatic amines. Unfortunately, the systems in question have the disadvantage that the range of colour tones is limited and that, when used in human beings, aromatic 1,2 15 diacetylated compounds cause very serious staining of the scalp. The problem addressed by the present invention was to provide colourants for keratin fibres, more especially human hair, which would be at least equivalent in quality to conventional oxidation hair dyes in regard to depth of colour, grey coverage and fastness properties, but which would not necessarily have to contain oxidising agents, such as H 2 0 2 for example. Another problem addressed 20 by the invention was to provide colourants with which a wide variety of colour tones could be obtained. Staining of the skin would be avoided. In addition, the colourants according to the invention would have very little, if any, sensitising potential. Accordingly, the present invention relates to the use of aromatic di- and oligoacyl compounds corresponding to formula (1): 0 R5 R1 R4 I R2 R3 25 O in which R 1 and R 2 independently of one another represent a lower (C 14 ) alkyl group, an aryl or heteroaryl group, R 3 , R 4 and R 5 independently of one another represent a hydrogen atom, a halogen atom, a C14 alkyl group, C14 alkoxy group or a hydroxy-(Cl4)-alkoxy group, a hydroxy group, nitro group, amino group or C14 acyl group, with the proviso that 1,2-diacetyl benzenes are excluded, in the 30 presence of at least one compound containing a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or at least one CH-active compound, for colouring keratin-containing fibres. It has surprisingly been found that combinations of the aromatic di- and oligoacyl compounds 35 defined above and amines or CH-active compounds are eminently suitable for colouring keratin- 3 containing fibres. They give colours with excellent brilliance and depth of colour and lead to a wide variety of shades. In principle, oxidising agents may be present although they are not necessary. In the context of the invention, keratin-containing fibres are understood to include wool, pelts, feathers and, in particular, human hair. In principle, however, the colourants according to the 5 invention may also be used to colour other natural fibres such as, for example, cotton, jute, sisal, linen or silk, modified natural fibres such as, for example, regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose and synthetic fibres such as, for example, polyamide, polyacrylonitrile, polyurethane and polyester fibres. The present invention also encompasses the use of substances which represent reaction 10 products of the individual components with one another. The present invention also relates to a preparation for colouring keratin-containing fibres, more especially human hair, which contains one or more aromatic di- and oligoacyl compounds corresponding to formula (1) above and at least one compound containing a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, 15 nitrogen-containing heterocyclic compounds, amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or at least one CH-active compound. Suitable compounds of formula (1) which may be used as component A are 1,3 diacetylbenzene, 1,4-diacetylbenzene, 1,3,5-triacetylbenzene, 2-benzoylacetophenone, 2-(4 methoybenzoyl)-acetophenone, 2-(2-furoyl)-acetophenone, 2-(2-pyridoyl)-acetophenone and 2-(3 20 pyridoyl)-acetophenone and mixtures thereof, 1,4-diacetylbenzene, 2-(2-furoyl)-acetophenone and 2 (3-pyridoyl)-acetophenone being preferred. Suitable compounds containing a primary or secondary amino group for component B are, for example, primary aromatic amines, such as N,N-dimethyl-, N,N-diethyl-, N-(2-hydroxyethyl)-N-ethyl-, N,N-bis-(2-hydroxyethyl)-, N-(2-methoxyethyl)-, 2,3-, 2,4-, 2,5-dichloro-p-phenylenediamine, 2-chloro 25 p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline dihydrobromide, 2-, 3-, 4-aminophenol, 2 aminomethyl-4-aminophenol, 2-hydroxymethyl-4-aminophenol, o-, p-phenylenediamine, o-, m toluylenediamine, 2,5-diaminotoluene, -phenol, -phenethol, 4-amino-3-methylphenol, 2-(2,5 diaminophenyl)-ethanol, 2-(2,4-diaminophenoxy)-ethanol, 2-(2,5-diaminophenoxy)-ethanol, 4 methylamino-, 3-amino-4-(2'-hydroxyethyloxy)-, 3,4-methylenediamino-, 3,4-methylenedioxyaniline, 3 30 amino-2,4-dichloro-, 4-methylamino-, 2-methyl-5-amino-, 3-methyl-4,-amino-, 2-methyl-5-(2 hydroxyethylamino)-, 6-methyl-3-amino-2-chloro-, 2-methyl-5-amino-4-chloro-, 3,4-methylenedioxy-, 5-(2-hydroxyethylamino)-4-methoxy-2-methylphenol, 4-amino-2-hydroxymethylphenol, 1,3-diamino 2,4-dimethoxybenzene, 2-, 3-, 4-aminobenzoic acid, -phenylacetic acid, 2,3-, 2,4-, 2,5-, 3,4-, 3,5 diaminobenzoic acid, 4-, 5-aminosalicylic acid, 3-amino-4-hydroxy-, 4-amino-3-hydroxybenzoic acid, 35 2-, 3-, 4-aminobenzenesulfonic acid, 3-amino-4-hydroxybenzenesulfonic acid, 4-amino-3 hydroxynaphthalene-1-sulfonic acid, 6-amino-7-hydroxynaphthalene-2-sulfonic acid, 7-amino-4 hydroxynaphthalene-2-sulfonic acid, 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid, 3-amino-2 naphthoic acid, 3-aminophthalic acid, 5-aminoisophthalic acid, 1,3,5-, 1,2,4-triaminobenzene, 1,2,4,5 tetraaminobenzene, 2,4,5-triaminophenol, pentaaminobenzene, hexaaminobenzene, 2,4,6 40 triaminoresorcinol, 4,5-diaminopyrocatechol, 4,6-diaminopyrogallol, 3,5-diamino-4- 4 hydroxypyrocatechol, aromatic anilines and phenols containing another aromatic radical corresponding to formula ll:
R
6
R
9 R8' XO R1 0 R11 in which R6 is a hydroxy group or an amino group which may be substituted by C 1 4 alkyl, C14 5 hydroxyalkyl or C1A-alkoxy-C1A-alkyl groups, R 7 , R 8 , R 9 , R 1 0 and R 11 represent hydrogen, a hydroxy group or an amino group which may be substituted by C14 alkyl, C14 hydroxyalkyl, C14 aminoalkyl or C14-alkoxy-C14-alkyl groups or a carboxylic or sulfonic acid group and X is a direct bond, a saturated or unsaturated optionally hydroxy-substituted carbon chain containing 1 to 4 carbon atoms, a carbonyl, sulfonyl or imino group, an oxygen or sulfur atom or a group corresponding to formula IlIl: 10 Z-(CH 2
-Y-CH
2 -Z')o (Ill) in which Y is a direct bond, a CH2 or CHOH group, Z and Z' independently of one another represent an oxygen atom, an NR 1 2 group, where R 1 2 is hydrogen, a C14 alkyl or a hydroxy-Cl-4-alkyl group, the group 0-(CH2)p-NH or NH-(CH2)p--O, where p and p' = 2 or 3, and o is a number of 1 to 4, such as for example 4,4'-diaminostilbene, 4,4'-diaminostilbene-2,2'-disulfonic acid monosodium or disodium salt, 15 4,4'-diaminodiphenyl methane, -sulfide, -sulfoxide, -amine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, -diphenyl ether, 3,3',4,4'-tetraaminodiphenyl, 3,3'4,4' tetraaminobenzophenone, 1,3-bis-(2,4-diaminophenoxy)-propane, 1,8-bis-(2,5-diaminophenoxy)-3,6 dioxaoctane, 1,3-bis-(4-aminophenylamino)-propane, -2-propanol, 1,3-bis-[N-(4-aminophenyl)-2 hydroxyethylaminoj-2-propanol, N,N-bis-[2-(4-aminophenoxy)-ethyl]-methylamine, N-phenyl-1,4 20 phenylenediamine. The compounds mentioned above may be used both in free form and in the form of their physiologically compatible salts, more especially as salts of inorganic acids, such as hydrochloric acid or sulfuric acid. Suitable nitrogen-containing heterocyclic compounds are, for example, 2-, 3-, 4-amino-, 2 25 amino-3-hydroxy-, 2,6-diamino-, 2,5-diamino-, 2,3-diamino-, 2-dimethylamino-5-amino-, 2 methylamino-3-amino-6-methoxy-, 2,3-diamino-6-methoxy-, 2,6-dimethoxy-3,5-diamino-, 2,4,5 triamino-, 2,6-dihydroxy-3,4-dimethyl pyridine, 2,4-dihydroxy-5,6-diamino-, 4,5,6-triamino-, 4-hydroxy 2,5,6-triamino-, 2-hydroxy-4,5,6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino-4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-amino-4-methoxy-6-methyl pyrimidine, 3,5-diaminopyrazole, -1,2,4-triazole, 3-amino-, 30 3-amino-5-hydroxypyrazole, 2-, 3-, 8-aminoquinoline, 4-aminoquinaldine, 2-, 6-aminonicotinic acid, 5 aminoisoquinoline, 5-, 6-aminoindazole, 5-, 7-aminobenzimidazole, -benzothiazole, 2,5-dihydroxy-4 morpholinoaniline and indole and indoline derivatives, such as 4-, 5-, 6-, 7-aminoindole, 5,6 dihydroxyindole, 5,6-dihydroxyindoline and 4-hydroxyindoline. The compounds mentioned above may be used both in free form and in the form of their physiologically compatible salts, for example as salts 35 of inorganic acids, such as hydrochloric acid or sulfuric acid. Suitable amino acids are any naturally occurring and synthetic amino acids, for example the amino acids obtainable by hydrolysis from vegetable or animal proteins, for example collagen, keratin, 5 casein, elastin, soya protein, wheat gluten or almond protein. Both acidic and alkaline amino acids may be used. Preferred amino acids are arginine, histidine, tyrosine, phenyl alanine, DOPA (dihydroxyphenyl alanine), ornithine, lysine and tryptophane. The oligopeptides may be naturally occurring or synthetic oligopeptides and the oligopeptides 5 present in polypeptide or protein hydrolysates providing they are sufficiently soluble in water for use in the colourants according to the invention. Examples of such polypeptides are glutathione and the oligopeptides present in the hydrolysates of collagen, keratin, casein, elastin, soya protein, wheat gluten or almond protein. These oligopeptides are preferably used together with compounds containing a primary or secondary amino group or with aromatic hydroxy compounds. 10 Suitable aromatic hydroxy compounds are, for example, 2-, 4-, 5-methyl resorcinol, 2,5 dimethyl resorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-, 3-, 4-methoxy-, 3-dimethylamino-, 2-(2-hydroxyethyl)-, 3,4 methylenedioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, -phenylacetic acid, gallic acid, 2,4,6 trihydroxybenzoic acid, -acetophenone, 2-, 4-chlororesorcinol, 1-naphthol, 1,5-, 2,3-, 2,7 15 dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthalene sulfonic acid, 3,6-dihydroxy-2,7 naphthalene sulfonic acid. Examples of CH-active compounds are 1,2,3,3-tetramethyl-3H-indolium iodide, 1,2,3,3 tetraamethyl indolium-p-toluene sulfonate, 1,2,3,3-tetramethyl-3H-indolium methane sulfonate, Fischer's base (1,3,3-trimethyl-2-methylindoline), 2,3-dimethylbenzothiazolium iodide, 2,3 20 dimethylbenzothiazolium-p-toluene sulfonate, rhodamine, rhodamine-3-acetic acid, 1-ethyl-2 quinaldinium iodide, 1-methyl-2-quinaldinium iodide, barbituric acid, thiobarbituric acid, 1,3-dimethyl thiobarbituric acid, diethyl thiobarbituric acid, oxindole, 3-indoxyl acetate, coumaranone and 1-methyl 3-phenyl-2-pyrazolinone. In all colourants, several different colouring substances may also be used together. Similarly, 25 several different components from the groups of compounds containing a primary or secondary amino group, nitrogen-containing heterocycles, aromatic hydroxy compounds or amino acids may be used together providing they do not impair the strengthening effect required in accordance with the invention of the added substances. Oxidising agents, for example H 2 0 2 , need not present where the aromatic di- and oligoacyl 30 compounds corresponding to formula (1) are used in accordance with the invention. However, it may be desirable in some cases to add hydrogen peroxide or other oxidising agents to the preparations according to the invention to obtain shades which are lighter than the keratin-containing fibres to be coloured. Oxidising agents are generally used in a quantity of 0.01 to 6wt%, based on the solution applied. A preferred oxidising agent for human hair is H 2 0 2 . 35 The colourants according to the invention produce a broad range of colour tones in the range from yellow-orange to brown-black; their fastness properties are good and the sensitising potential very low. In one preferred embodiment, the colourants according to the invention contain typical substantive dyes, for example from the group of nitrophenylenediamines, nitroaminophenols, azo 40 dyes, anthraquinones or indophenols, in addition to the compounds present in accordance with the 6 invention in order further to modify the colour tones. Preferred substantive dyes are the compounds known under the international names or commercial names of HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, 5 Disperse Black 9, Basic Brown 16 and Basic Brown 17 and also 4-amino-2-nitrodiphenylamine-2' carboxylic acid, 6-nitro-1,2,3,4-tetrahydroquinoxaline, hydroxyethyl-2-nitrotoluidine, picramic acid, 2 amino-6-chloro-4-nitrophenol, 4-ethylamino-3-nitrobenzoic acid and 2-chloro-6-ethylamino-1-hydroxy 4-nitrobenzene. The preparations according to the invention in this embodiment contain the substantive dyes in a quantity of, preferably, 0.01 to 20wt%, based on the colourant as a whole. 10 In addition, the preparations according to the invention may also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, camomile blossom, sandalwood, black tea, black alder bark, sage, logwood, madder root, catechu, sedre and alkanet. Other dye components present in the colourants according to the invention may be indoles and indolines and physiologically compatible salts thereof. Preferred examples are 5,6-dihydroxyindole, 15 N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propyl-5,6-dihydroxyindole, N-butyl-5,6 dihydroxyindole, 6-hydroxyindole, 6-aminoindole and 4-aminoindole. Also preferred are 5,6 dihydroxyindoline, N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6 dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, 6-hydroxyindoline, 6-aminoindoline and 4 aminoindoline. 20 The oxidation dye precursors or the substantive dyes present, if any, do not have to be single compounds. Instead, the hair colourants according to the invention - due to the processes used for producing the individual dyes - may contain small quantities of other components providing they do not adversely affect the colouring result or have to be ruled out for other reasons, for example toxicological reasons. 25 The colourants according to the invention produce intensive colours even at physiologically compatible temperatures of <450C. Accordingly, they are particularly suitable for colouring human hair. For application to human hair, the colourants are normally incorporated in a water-containing cosmetic carder. Suitable water-containing cosmetic carriers are, for example, creams, emulsions, gels or even surfactant-containing foaming solutions, for example shampoos or other formulations 30 suitable for application to the keratin-containing fibres. If necessary, the colourants may even be incorporated in water-free carriers. The colourants according to the invention may also contain any of the known active substances, additives and auxiliaries typical of such formulations. In many cases, the colourants contain at least one surfactant, both anionic and zwitterionic, ampholytic, nonionic and cationic 35 surfactants being suitable in principle. In many cases, however, it has been found to be of advantage to select the surfactants from anionic, zwitterionic or nonionic surfactants. Suitable anionic surfactants for the preparations according to the invention are any anionic surface-active substances suitable for use on the human body. Such substances are characterised by a water-solubilising anionic group such as, for example, a carboxylate, sulfate, sulfonate or 40 phosphate group and a lipophilic alkyl group containing around 10 to 22 carbon atoms. In addition, 7 glycol or polyglycol ether groups, ester, ether, amide groups and hydroxyl groups may also be present in the molecule. The following are examples of suitable anionic surfactants - in the form of the sodium, potassium and ammonium salts and the mono-, di- and trialkanolammonium salts containing 2 or 3 carbon atoms in the alkanol group: 5 - linear fatty acids containing 10 to 22 carbon atoms (soaps), - ether carboxylic acids corresponding to the formula R-O-(CH2-CH20)x-CH2-COOH, in which R is a linear alkyl group containing 10 to 22 carbon atoms and x = 0 or I to 16, - acyl sarcosides containing 10 to 18 carbon atoms in the acyl group, - acyl taurides containing 10 to 18 carbon atoms in the acyl group, 10 - acyl isethionates containing 10 to 18 carbon atoms in the acyl group, - sulfosuccinic acid mono- and dialkyl esters containing 8 to 18 carbon atoms in the alkyl group and sulfosuccinic acid monoalkyl polyoxyethyl esters containing 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, - linear alkane sulfonates containing 12 to 18 carbon atoms, 15 - linear a-olefin sulfonates containing 12 to 18 carbon atoms, - cc-sulfofatty acid methyl esters of fatty acids containing 12 to 18 carbon atoms, - alkyl sulfates and alkyl polyglycol ether sulfates corresponding to the formula R-O(CH 2
-CH
2 0)x
SO
3 H, in which R is a preferably linear alkyl group containing 10 to 18 carbon atoms and x = 0 or 1 to 12, 20 - mixtures of surface-active hydroxysulfonates according to DE-A-37 25 030, - sulfated hydroxyalkyl polyethylene and/or hydroxyalkylene propylene glycol ethers according to DE-A-37 23 354, - sulfonates of unsaturated fatty acids containing 12 to 24 carbon atoms and 1 to 6 double bonds according to DE-A-39 26 344, 25 - esters of tartaric acid and citric acid with alcohols in the form of addition products of around 2 to 15 molecules of ethylene oxide and/or propylene oxide with fatty alcohols containing 8 to 22 carbon atoms. Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids containing 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups 30 in the molecule and, in particular, salts of saturated and, more particularly, unsaturated C 8 22 carboxylic acids, such as oleic acid, stearic acid, isostearic acid and palmitic acid. In the context of the invention, zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one -COO) or -S0 3 (-) group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines, such as N-alkyl 35 N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl ammonium glycinate, N acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethy imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate. A preferred zwitterionic surfactant is the fatty acid amide derivative known by the CTFA name of 40 Cocamidopropyl Betaine.
8 Ampholytic surfactants are surface-active compounds which, in addition to a C8.18 alkyl or acyl group, contain at least one free amino group and at least one -COOH or -SO 3 H group in the molecule and which are capable of forming inner salts, Examples of suitable ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkyl aminobutyric acids, N-alkyl iminodipropionic acids, N 5 hydroxyethyl-N-alkyl amidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkyl aminopropionic acids and alkyl aminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-cocoalkyl aminopropionate, cocoacyl aminoethyl aminopropionate and C12-18 acyl sarcosine. Nonionic surfactants contain, for example, a polyol group, a polyalkylene glycol ether group or a 10 combination of polyol and polyglycol ether groups as the hydrophilic group. Examples of such compounds are - products of the addition of 2 to 30 moles of ethylene oxide and/or 0 to 5 moles of propylene oxide onto linear fatty alcohols containing 8 to 22 carbon atoms, onto fatty acids containing 12 to 22 carbon atoms and onto alkylphenols containing 8 to 15 carbon atoms in the alkyl group, 15 - C12.22 fatty acid monoesters and diesters of products of the addition of 1 to 30 moles of ethylene oxide onto glycerol, - C.22 alkyl mono- and oligoglycosides and ethoxylated analogues thereof, - products of the addition of 5 to 60 moles of ethylene oxide onto castor oil and hydrogenated castor oil, 20 - products of the addition of ethylene oxide onto sorbitan fatty acid esters, - products of the addition of ethylene oxide onto fatty acid alkanolamides. Examples of cationic surfactants suitable for use in the hair treatment formulations according to the invention are, in particular, quaternary ammonium compounds. Preferred quaternary ammonium compounds are ammonium halides, such as alkyl trimethyl ammonium chlorides, dialkyl dimethyl 25 ammonium chlorides and trialkyl methyl ammonium chlorides, for example cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammonium chloride. Other cationic surfactants suitable for use in accordance with the invention are the quaternised protein hydrolysates. 30 Also suitable for use in accordance with the invention are cationic silicone oils such as, for example, the commercially available products Q2-7224 (manufacturer: Dow Corning; a stabilised trimethyl silyl amodimethicone), Dow Corning 929 Emulsion (containing a hydroxyamino-modified silicone which is also known as Amodimethicone), SM-2059 (manufacturer: General Electric), SLM 55067 (manufacturer: Wacker) and Abil@-Quat 3270 and 3272 (manufacturer: Th. Goldschmidt; 35 diquaternary polydimethyl siloxanes, Quaternium-80). Alkyl amidoamines, particularly fatty acid amidoamines, such as the stearyl amidopropyl dimethyl amine obtainable as Tego Amid@S 18, are distinguished not only by their favourable conditioning effect, but also and in particular by their ready biodegradability.
9 Quaternary ester compounds, so-called "esterquats", such as the dialkyl ammonium methosulfates and methyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketed under the trade name of Stepantex@, are also readily biodegradable. One example of a quaternary sugar derivative suitable for use as a cationic surfactant is the 5 commercially available product Glucquat@100 (CTFA name: Lauryl Methyl Gluceth-10 Hydroxypropyl Diammonium Chloride). The compounds containing alkyl groups used as surfactants may be single compounds. In general, however, these compounds are produced from native vegetable or animal raw materials so that mixtures with different alkyl chain lengths dependent upon the particular raw material are 10 obtained. The surfactants representing addition products of ethylene and/or propylene oxide with fatty alcohols or derivatives of these addition products may be both products with a "normal" homologue distribution and products with a narrow homologue distribution. Products with a "normal" homologue distribution are mixtures of homologues which are obtained in the reaction of fatty alcohol and 15 alkylene oxide using alkali metals, alkali metal hydroxides or alkali metal alcoholates as catalysts. By contrast, narrow homologue distributions are obtained when, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homologue distribution can be of advantage. Other active substances, auxiliaries and additives are, for example, 20 - nonionic polymers such as, for example, vinyl pyrrolidone/vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone/vinyl acetate copolymers and polysiloxanes, - cationic polymers, such as quaternised cellulose ethers, polysiloxanes containing quaternary groups, dimethyl diallyl ammonium chloride polymers, acrylamide/dimethyl diallyl ammonium chloride copolymers, dimethyl aminoethyl methacrylate/vinyl pyrrolidone copolymers quaternised with diethyl 25 sulfate, vinyl pyrrolidone/imidazolinium methochloride copolymers and quaternised polyvinyl alcohol, - zwitterionic and amphoteric polymers such as, for example, acrylamidopropyl/trimethyl ammonium chloride/acrylate copolymers and octyl acrylamide/methyl methacrylate/tert. butyl aminoethyl methacrylate/2-hydroxypropyl methacrylate copolymers, - anionic polymers such as, for example, polyacrylic acids, crosslinked polyacrylic acids, vinyl 30 acetate/crotonic acid copolymers, vinyl pyrrolidonelvinyl acrylate copolymers, vinyl acetate/butyl maleate/ isobornyl acrylate copolymers, methyl vinyl ether/maleic anhydride copolymers and acrylic acid/ethyl acrylate/N-tert. butyl acrylamide terpolymers, - thickeners, such as agar agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, linseed gums, dextrans, cellulose derivatives, for example methyl cellulose, as hydroxyalkyl cellulose and carboxymethyl cellulose, starch fractions and derivatives, such as amylose, amylopectin and dextrins, clays such as, for example, bentonite or fully synthetic hydrocolloids such as, for example, polyvinyl alcohol, - structurants, such as glucose and maleic acid, - hair-conditioning compounds, such as phospholipids, for example soya lecithin, egg lecithin and 40 kephalins, and also silicone oils, 10 - protein hydrolysates, more particularly elastin, collagen, keratin, milk protein, soya protein and wheat protein hydrolysates, condensation products thereof with fatty acids and quaternised protein hydrolysates, - perfume oils, dimethyl isosorbide and cyclodextrins, 5 - solubilisers, such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, - antidandruff agents, such as Piroctone Olamine and Zinc Omadine, - other substances for adjusting the pH value, - active substances, such as panthenol, pantothenic acid, allantoin, pyrrolidone carboxylic acids 10 and salts thereof, plant extracts and vitamins,
-
cholesterol,
-
UV filters, - consistency factors, such as sugar esters, polyol esters or polyol alkyl ethers, - fats and waxes, such as spermaceti, beeswax, montan wax, paraffins, fatty alcohols and fatty 15 acid esters, - fatty acid alkanolamides, - complexing agents, such as EDTA, NTA and phosphonic acids, - swelling and penetration agents, such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates, 20 imidazoles, tannins, pyrrole, - opacifiers, such as latex, - pearlescers, such as ethylene glycol mono- and distearate, - propellents, such as propane/butane mixtures, N 2 0, dimethyl ether, CO 2 and air and - antioxidants. 25 To produce the colourants according to the invention, the constituents of the water-containing carrier are used in the usual quantities for this purpose. For example, emulsifiers are used in concentrations of 0.5 to 30wt% while thickeners are used in concentrations of 0.1 to 25wt%, based on the colourant as a whole. It can be of advantage to the colouring result to add ammonium or metal salts to the colourants. 30 Suitable metal salts are, for example, formates, carbonates, halides, sulfates, butyrates, valerates, caproates, acetates, lactates, glycolates, tartrates, citrates, gluconates, propionates, phosphates and phosphonates of alkaline earth metals, such as potassium, sodium or lithium, alkaline earth metals, such as magnesium, calcium, strontium or barium, or of aluminium, manganese, iron, cobalt, copper or zinc, sodium acetate, lithium bromide, calcium bromide, calcium gluconate, zinc chloride, zinc 35 sulfate, magnesium chloride, magnesium sulfate, ammonium carbonate, chloride and acetate being preferred. These salts are preferably present in a quantity of 0.03 to 65mmol and more preferably in a quantity of 1 to 40mmol, based on 100 g of the colourant as a whole. The pH value of the ready-to-use colouring preparations is normally in the range from 2 to 11 and preferably in the range from 5 to 9.
11 In order to colour the keratin-containing fibres, more especially human hair, the colourants are generally applied to the hair in the form of the water-containing cosmetic carrier in a quantity of 100 g, left thereon for about 30 minutes and then rinsed out or washed out with a commercially available shampoo. 5 The compounds of components A and B may either be applied to the hair simultaneously or even successively, in which case it does not matter which of the two components is applied first. The ammonium or metal salts optionally present may be added to the first component or to the second component. A time of up to 30 minutes can be allowed to pass between application of the first component and application of the second component. The fibres may even be pretreated with the salt 10 solution. Components A and B of the preparations according to the invention may be stored either separately or together either in the form of a liquid or paste-like preparation (aqueous or water-free) or as a dry powder. If the components are stored together in a liquid preparation, the preparation in question should be substantially free from water to reduce any risk of the components reacting. 15 Where the reactive components are stored separately, they are mixed thoroughly together only shortly before application. Where the components are stored as a dry powder, a defined quantity of warm water (50 to 80 0 C) is normally added and a homogeneous mixture prepared before application. Examples Preparation of a colouring solution 20 A suspension of 10mmol of a colouring component, 10mmol of anm amine, 10mmol of sodium acetate and 1 drop of a 20% fatty alkyl ether sulfate solution in 100mL of water was prepared. The suspension was briefly heated to around 80*C and filtered after cooling, after which the pH value was adjusted to 6. One tress of 90% grey, non-pretreated human hair was placed in this colouring solution for 30 25 minutes at 300C. The coloured tress was then rinsed for 30 seconds with lukewarm water, dried in a stream of warm air (30-40*C) and then combed. The colours were visually evaluated in daylight. The particular shades and depths of colour are shown in Table 1 below. The depth of colour was evaluated on the following scale: - : very faint, if any, colour 30 (+) : weak intensity + : medium intensity +(+) :medium to strong intensity ++ : strong intensity ++(+) : strong to very strong intensity 35 +++ : very strong intensity Table 1 Colouring with 1,4-diacetyl benzene Component B Shade Depth of colour 2,5-Diaminotoluene x H 2
SO
4 Dark violet +++ 2,4,5,6-Tetraaminopyrimidine x H 2
SO
4 Dark yellow ++(+) 1,8-Bis-(2,5-diaminophenoxy)-3,6 dioxaoctane x 4HCI Grey-black |.+++ 2-Methylamino-3-amino-6-methoxy pyridine x 2HCI Black brown +++ 12 2-(2,5-Diaminophenyl)-ethanol x H 2 S0 4 Violet-brown ++ 2-Aminomethyl-4-aminophenol x 2HCI Yellow-brown +(+) N,N-bis-(2-hydroxyethyl)-p phenylenediamine x 2HCl Blue-black.. 4,4'-Diaminodiphenylamine x H 2 S0 4 Grey-brown ++ 2,6-Dimethoxy-3,5-diaminopyridine____________________ x 2HCl Black ... ______ Table 2 Colouring with_1,3,5-triacetyl benzene__________ Component B Shade Depth of colour 2,5-Diaminotoluene x H 2 S0 4 Grey-violet ++ 2,4,5,6-Tetraaminopydmidine x H 2 S0 4 Yellow +(+ 1 ,8-Bis-(2,5-diaminophenoxy)-3,6 dioxaoctane x 4 HCI Dark grey-green ++(+) 2-Methylamino-3-amino-6-methoxy pyridine x 2 HCI Black-brown.. 2-(2,5-Diaminophenyl)-ethanol x H 2 S0 4 Violet-grey ++(+ 2-Aminomethyl-4-aminophenol x 2HCI Mid-brown +(+ N,N-bis-(2-hydroxyethyl)-p-__________ phenylenediamine x 2HCI Yellow-grey +(+) 4,4'-Diaminodiphenylamine x H 2 S0 4 Blue-black__________ 2,6-Dimethoxy-3,5-diaminopyndine x 2HCI Blue-black________ Table 3 Colouring with 1,3-diacetyl benzene FComponent B Shade Depth of colour 2,5-Diaminotoluene x H 2 S0 4 Violet-brown ++ 2,4,5,6-Tetraaminopydmidine x H 2 S0 4 Olive-yellow + 1 ,8-Bis-(2,5-diaminophenoxy)-3,6-___________________ Sdioxaoctane x 4 HCI Grey ++(+ -2-Methylamino-3-amino-6-methoxy- _________ ____pyridine_________x_________ Dark brown+++ 2-(2,5-Diaminophenyl)-ethanol x H 2 S0 4 Ochre-grey ++ 2-Aminomethyl-4-aminophenol x 2HCl Light brown + -diamin x HCIOlive-grey ++ 4,4'-Diaminodiphenylamine x H 2 S0 4 Olive-green ++ 2,6-Dimethoxy-3,5-diaminopyridine___________________ x2HCl Blue-black ... ______ 6 Table 4 Colouring with_2(2furoyl)-acetophenone__________ Component B Shade :Depth of colour I Ethanolamine Yellow + [2,5-Diaminotoluene x H 2 S0 4 Dark brown -+ 2,4,5,6-Tetraaminopydmidine x H 2 S0 4 Mid-brown I ++ Table 5 Colouring with 2-(3-pyridoyl)-acetophenone__________ Component B Shade Depth oioourI~ 2,5-Diaminotoluene x H 2 S0 4 Brown+++ 2,4,5,6-Tetraaminoprimidine x H 2 S0 4 Orange-brown + 13 Table 6 Colouring with 2-(4-pyridoyl)-acetophenone Component B Shade Depth of colour L-(+)-Omithine x HCI Brown-green ++(+) 2,5-Diaminotoluene x H 2
SO
4 Violet-brown ++ 2,4,5,6-Tetraaminopyrimidine x H 2
SO
4 Orange-yellow +(+)
Claims (7)
1. The use of aromatic di- and oligoacy compounds corresponding to formula (1): 0 R5 R1 R4 I R2 R3 0 in which R 1 and R 2 independently of one another represent a lower (CiA) alkyl group, an aryl or 5 heteroaryl group, R 3 , R 4 and R 5 independently of one another represent a hydrogen atom, a halogen atom, a C1I alkyl group, CIA alkoxy group or a hydroxy-(C14)-alkoxy group, a hydroxy group, nitro group, amino group or C1A acyl group, with the proviso that 1,2-diacetyl benzenes are excluded, in the presence of at least one compound containing a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic 10 compounds, amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or at least one CH-active compound, for colouring keratin-containing fibres.
2. A preparation for colouring keratin-containing fibres, more particularly human hair, containing (A) one or more aromatic di- and oligoacyl compounds corresponding to formula (1): 0 R5 R1 R4 ( R2 R3 15 0 in which R 1 and R 2 independently of one another represent a lower (CIA) alkyl group, an aryl or heteroaryl group, R 3 , R 4 and R5 independently of one another represent a hydrogen atom, a halogen atom, a C14 alkyl group, CIA alkoxy group or a hydroxy-(C14)-alkoxy group, a hydroxy group, nitro group, amino group or CIA acyl group, with the proviso that 1,2-diacetyl benzenes are excluded, and 20 (B) at least one compound containing a primary or secondary amino group or hydroxy group selected from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or at least one CH-active compound. 2. A preparation as claimed in claim 2, characterised in that component A is selected from 25 the group consisting of 1,3-diacetyl benzene, 1,4-diacetyl benzene, 1,3,5-triacetyl benzene, 2-benzoyl acetophenone, 2-(4-methoxybenzoyl)-acetophenone, 2-(2-furoyl)-acetophenone, 2-(2-pyridoyl) acetophenone and 2-(3-pyridoyl)-acetophenone.
3. A preparation as claimed in claim 2 or 3, characterised in that the compounds of component B are selected from primary or secondary amines from the group consisting of N-(2 30 hydroxyethyl)-N-ethyl-, N-(2-methoxyethyl)-, 2,3-, 2,4-, 2,5-dichloro-p-phenylenediamine, 2-chloro-p phenylenediamine, N,N-bis-(2-hydroxyethyl)-p-phenylenediamine, 2,5-dihydroxy-4-morpholinoaniline 15 dihydrobromide, 2-, 3-, 4-aminophenol, o-, p-phenylenediamine, 2,4-diaminophenoxyethanol, 2-(2,5 diaminophenyl)-ethanol, 2,5-diaminotoluene, -phenol, -phenethol, 4-methylamino-, 3-amino-4-(2' hydroxyethyloxy)-, 3,4-methylenediamino-, 3,4-methylenedioxyaniline, 3-amino-2,4-dichloro-, 4 methylamino-, 3,4-methylenedioxy-, 3-methyl-4-amino-, 2-methyl-5-(2-hydroxyethylamino)-, 6-methyl 5 3-amino-2-chloro-, 5-(2-hydroxyethylamino)-4-methoxy-2-methyl-, 4-amino-2-aminomethyl phenol, 4 amino-2-hydroxymethyl phenol, 3,4-methylenedioxyphenol, 1,3-diamino-2,4-dimethoxybenzene, 2-, 3 , 4-aminobenzoic acid, -phenylacetic acid, 2,3-, 2,4-, 2,5-, 3,4-, 3,5-diaminobenzoic acid, 4-, 5 aminosalicylic acid, 3-amino-4-hydroxy-, 4-amino-3-hydroxybenzoic acid, 2-, 3-, 4 aminobenzenesulfonic acid, 3-amino-4-hydroxybenzenesulfonic acid, 4-amino-3-hydroxynaphthalene 10 1-sulfonic acid, 6-amino-7-hydroxynaphthalene-2-sulfonic acid, 7-amino-4-hydroxynaphthalene-2 sulfonic acid, 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid, 3-amino-2-naphthoic acid, 3 aminophthalic acid, 5-aminoisophthalic acid, 1,3,5-, 1,2,4-triaminobenzene, 1,2,4,5 tetraaminobenzene tetrahydrochloride, 2,4,5-triaminophenol trihydrochloride, pentaaminobenzene pentahydrochloride, hexaaminobenzene hexahydrochloride, 2,4,6-triaminoresorcinol trihydrochloride, 15 4,5-diaminopyrocatechol sulfate, 4,6-diaminopyrogallol dihydrochloride, 3,5-diamino-4 hydroxypyrocatechol sulfate, aromatic anilines and phenols containing another aromatic radical, such as 4,4'-diaminostilbene dihydrochloride, 4,4'-diaminostilbene-2,2'-disulfonic acid sodium salt, 4,4' diaminodiphenyl methane, -sulfide, -sulfoxide, -amine, 4,4'-diaminodiphenylamine-2-sulfonic acid, 4,4'-diaminobenzophenone, -diphenyl ether, 3,3',4,4'-tetraaminodiphenyl tetrahydrochlorde, 3,3'4,4' 20 tetraaminobenzophenone, 1,3-bis-(2,4-diaminophenoxy)-propane tetrahydrochloride, 1,3-bis-(2,5 diaminophenoxy)-3,6-dioxaoctane tetrahydrochloride, 1,3-bis-(4-aminophenylamino)-propane, -2 propanol, 1,3-bis-[N-(4-aminophenyl)-2-hydroxyethylamino]-2-propanol, N,N-bis-[2-(4-aminophenoxy) ethyl]-methylamine trihydrochloride; nitrogen-containing heterocyclic compounds selected from the group consisting of 2-, 3-, 4-amino-, 2-amino-3-hydroxy-, 3-amino-2-hydroxy-, 2,6-diamino-, 2,5 25 diamino-, 2,3-diamino-, 2-dimethylamino-5-amino-, 3-amino-2-methylamino-6-methoxy-, 2,3-diamino
6-methoxy-, 3,5-diamino-2,6-dimethoxy-, 2,4,5-triamino-, 2,6-dihydroxy-3,4-dimethyl pyridine, 4,5,6 triamino-, 2-hydroxy-4,5,6-triamino-, 4-hydroxy-2,5,6-triamino-, 2,4,5,6-tetraamino-, 2-methylamino 4,5,6-triamino-, 2,4-, 4,5-diamino-, 2-amino-4-methoxy-6-methyl pyrimidine, 2,3,4-trimethyl pyrrole, 2,4-dimethyl-3-ethyl pyrrole, 3,5-diaminopyrazole, -1,2,4-triazole, 3-amino-, 3-amino-5 30 hydroxypyrazole, 2-, 3-, 8-aminoquinoline, 4-aminoquinaldine, 2-, 6-aminonicotinic acid, 5 aminoisoquinoline, 5-, 6-aminoindazole, 5-, 7-aminobenzimidazole, -benzothiazole, 2,5-dihydroxy-4 morpholinoaniline and indole and indoline derivatives, such as 4-, 5-, 6-, 7-aminoindole, 4-, 5-, 6-, 7 hydroxyindole, 5,6-dihydroxyindole, 5,6-dihydroxyindoline and 4-hydroxyindoline and physiologically compatible salts of these compounds formed with preferably inorganic acids; aromatic hydroxy 35 compounds selected from the group consisting of 2-, 4-, 5-methyl resorcinol, 2,5-dimethyl resorcinol, resorcinol, 3-methoxyphenol, pyrocatechol, hydroquinone, pyrogallol, phloroglucinol, hydroxyhydroquinone, 2-, 3-, 4-methoxy-, 3-dimethylamino-, 2-(2-hydroxyethyl)-, 3,4 methylenedioxyphenol, 2,4-, 3,4-dihydroxybenzoic acid, -phenylacetic acid, gallic acid, 2,4,6 trihydroxybenzoic acid, -acetophenone, 2-, 4-chlororesorcinol, 1-naphthol, 1,5-, 2,3-, 2,7 40 dihydroxynaphthalene, 6-dimethylamino-4-hydroxy-2-naphthalene sulfonic acid, 3,6-dihydroxy-2,7- 16 naphthalene sulfonic acid and CH-active compounds selected from the group consisting of 1,2,3,3 tetramethyl-3H-indolium iodide, 1,2,3,3-tetraamethyl-3-indolium-p-toluene sulfonate, 1,2,3,3 tetramethyl-3-indolium methane sulfonate, 2,3-dimethylbenzothiazolium iodide, 2,3 dimethylbenzothiazolium-p-toluene sulfonate, rhodamine, rhodamine-3-acetic acid, 1-ethyl(methyl)-2 5 quinaldinium iodide, barbituric acid, thiobarbituric acid, 1,3-dimethyl(ethyl) thiobarbituric acid, oxindole, coumaranone and 1-methyl-3-phenyl-2-pyrazolinone. 5. A preparation as claimed in any of claims 2 to 4, characterised in that the compounds of components A and B are each used in a quantity of 0.03 to 65mmol and more particularly 1 to 40mmol, based on 100g of the colourant as a whole. 10 6. A preparation as claimed in any of claims 2 to 5, characterised in that oxidising agents are used in a quantity of 0.01 to 6wt%, based on the solution applied.
7. A preparation as claimed in any of claims 2 to 6, characterised in that H 2 0 2 is used as the oxidising agent.
8. A preparation as claimed in any of claims 2 to 7, characterised in that anionic, 15 zwitterionic and/or nonionic surfactants are used.
9. A process for colouring keratin-containing fibres, characterised in that a colourant containing (A) one or more aromatic di- and oligoacyl compounds corresponding to formula (1): 0 R5 R1 R4 (1 R3 R2 0 20 in which R 1 and R 2 independently of one another represent a lower (C1-4) alkyl group, an aryl or heteroaryl group, R 3 , R 4 and R5 independently of one another represent a hydrogen atom, a halogen atom, a C 14 alkyl group, C 1 4 alkoxy group or a hydroxy-(C14)-alkoxy group, a hydroxy group, nitro group, amino group or C 1 4 acyl group, with the proviso that 1,2-diacetyl benzenes are excluded, and (B) at least one compound containing a primary or secondary amino group or hydroxy group selected 25 from primary or secondary aliphatic or aromatic amines, nitrogen-containing heterocyclic compounds, amino acids, oligopeptides made up of 2 to 9 amino acids and aromatic hydroxy compounds and/or at least one CH-active compound, and typical cosmetic ingredients is applied to the keratin-containing fibres, left thereon for a time, usually about 30 minutes, and then rinsed out again or washed out with a shampoo.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1997131400 DE19731400A1 (en) | 1997-07-22 | 1997-07-22 | Use of di- and oligoacyl aromatics for dyeing keratin fibers |
DE19731400 | 1997-07-22 | ||
PCT/EP1998/004332 WO1999004754A1 (en) | 1997-07-22 | 1998-07-13 | Use of di- and oligoacylaromats for colouring fibres containing keratin |
Publications (1)
Publication Number | Publication Date |
---|---|
AU8542198A true AU8542198A (en) | 1999-02-16 |
Family
ID=7836486
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU85421/98A Abandoned AU8542198A (en) | 1997-07-22 | 1998-07-13 | Use of di- and oligoacylaromats for colouring fibres containing keratin |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0998256A1 (en) |
JP (1) | JP2001510782A (en) |
AU (1) | AU8542198A (en) |
DE (1) | DE19731400A1 (en) |
WO (1) | WO1999004754A1 (en) |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5628799A (en) * | 1991-09-26 | 1997-05-13 | Clairol Incorporated | Hair dying methods and kits which contain a dopa species, reactive direct dye, and a ferricyanide oxidant |
-
1997
- 1997-07-22 DE DE1997131400 patent/DE19731400A1/en not_active Withdrawn
-
1998
- 1998-07-13 EP EP98936419A patent/EP0998256A1/en not_active Withdrawn
- 1998-07-13 JP JP2000503815A patent/JP2001510782A/en active Pending
- 1998-07-13 AU AU85421/98A patent/AU8542198A/en not_active Abandoned
- 1998-07-13 WO PCT/EP1998/004332 patent/WO1999004754A1/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
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EP0998256A1 (en) | 2000-05-10 |
JP2001510782A (en) | 2001-08-07 |
WO1999004754A1 (en) | 1999-02-04 |
DE19731400A1 (en) | 1999-01-28 |
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